CN116969937A - Bcl-2抑制剂 - Google Patents

Info

Publication number

CN116969937A

CN116969937A CN202310560508.6A CN202310560508A CN116969937A CN 116969937 A CN116969937 A CN 116969937A CN 202310560508 A CN202310560508 A CN 202310560508A CN 116969937 A CN116969937 A CN 116969937A

Authority

CN

China

Prior art keywords

azaspiro

isopropylphenyl

nonane

butyl

mmol

Prior art date

2020-04-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• 229940123711 Bcl2 inhibitor Drugs 0.000 title description 8
• 239000012664 BCL-2-inhibitor Substances 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 100
• 238000000034 method Methods 0.000 claims abstract description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
• 201000010099 disease Diseases 0.000 claims abstract description 22
• 230000001640 apoptogenic effect Effects 0.000 claims abstract description 6
• 230000002074 deregulated effect Effects 0.000 claims abstract description 6
• -1 -C 3-10 Cycloalkyl Chemical group 0.000 claims description 552
• 125000000623 heterocyclic group Chemical group 0.000 claims description 78
• 125000000217 alkyl group Chemical group 0.000 claims description 77
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• 125000005605 benzo group Chemical group 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical group 0.000 claims description 24
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
• 125000001475 halogen functional group Chemical group 0.000 claims description 14
• 238000006467 substitution reaction Methods 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
• 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 abstract description 31
• 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 abstract description 29
• 102220346888 c.307G>T Human genes 0.000 abstract description 7
• 230000002401 inhibitory effect Effects 0.000 abstract description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 518
• 239000000203 mixture Substances 0.000 description 483
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 346
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 341
• 239000000243 solution Substances 0.000 description 310
• 239000011734 sodium Substances 0.000 description 271
• 230000002829 reductive effect Effects 0.000 description 242
• 235000019439 ethyl acetate Nutrition 0.000 description 172
• 238000005481 NMR spectroscopy Methods 0.000 description 162
• 239000012267 brine Substances 0.000 description 158
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 157
• DMUXSGAKEXSNGN-UHFFFAOYSA-N 2-ethyloctanoic acid Chemical compound CCCCCCC(CC)C(O)=O DMUXSGAKEXSNGN-UHFFFAOYSA-N 0.000 description 150
• 239000000543 intermediate Substances 0.000 description 145
• 239000007787 solid Substances 0.000 description 144
• 239000003921 oil Substances 0.000 description 143
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 131
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 114
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 113
• 238000004440 column chromatography Methods 0.000 description 106
• 239000003480 eluent Substances 0.000 description 104
• 239000012044 organic layer Substances 0.000 description 104
• 239000000741 silica gel Substances 0.000 description 103
• 229910002027 silica gel Inorganic materials 0.000 description 103
• 239000004698 Polyethylene Substances 0.000 description 102
• 239000011541 reaction mixture Substances 0.000 description 102
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 101
• 239000012074 organic phase Substances 0.000 description 95
• 229920006395 saturated elastomer Polymers 0.000 description 86
• 238000006243 chemical reaction Methods 0.000 description 84
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 76
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 76
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 76
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 68
• ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 64
• BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 64
• 238000000746 purification Methods 0.000 description 54
• 239000012043 crude product Substances 0.000 description 50
• 239000000460 chlorine Substances 0.000 description 43
• 125000005842 heteroatom Chemical group 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
• 230000015572 biosynthetic process Effects 0.000 description 29
• 238000003786 synthesis reaction Methods 0.000 description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
• 239000002904 solvent Substances 0.000 description 26
• 125000002950 monocyclic group Chemical group 0.000 description 25
• 238000001816 cooling Methods 0.000 description 23
• 229910052760 oxygen Inorganic materials 0.000 description 23
• 238000002953 preparative HPLC Methods 0.000 description 23
• 229910004373 HOAc Inorganic materials 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 238000003756 stirring Methods 0.000 description 21
• 125000002619 bicyclic group Chemical group 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 229910052717 sulfur Inorganic materials 0.000 description 18
• 229910052757 nitrogen Inorganic materials 0.000 description 17
• 239000001301 oxygen Substances 0.000 description 16
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 229910052799 carbon Inorganic materials 0.000 description 14
• 230000035772 mutation Effects 0.000 description 14
• 238000004808 supercritical fluid chromatography Methods 0.000 description 14
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 13
• 206010028980 Neoplasm Diseases 0.000 description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
• 125000004432 carbon atom Chemical group C* 0.000 description 13
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
• 201000011510 cancer Diseases 0.000 description 10
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
• 208000035475 disorder Diseases 0.000 description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 230000014759 maintenance of location Effects 0.000 description 10
• 239000012071 phase Substances 0.000 description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
• GVHWFXNONFYORH-UHFFFAOYSA-N C(C)(C)C1=C(C=CC=C1)C1N(C(CNC1)=O)C1CC2(C1)CCN(CC2)C(=O)OC(C)(C)C Chemical compound C(C)(C)C1=C(C=CC=C1)C1N(C(CNC1)=O)C1CC2(C1)CCN(CC2)C(=O)OC(C)(C)C GVHWFXNONFYORH-UHFFFAOYSA-N 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 238000004128 high performance liquid chromatography Methods 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 8
• 102220025226 rs74315455 Human genes 0.000 description 8
• 239000011593 sulfur Chemical group 0.000 description 8
• 238000005406 washing Methods 0.000 description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
• 239000011737 fluorine Substances 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
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• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
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• 230000000694 effects Effects 0.000 description 6
• 238000000605 extraction Methods 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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• WXSFUHRFTJTOCA-UHFFFAOYSA-N C(C)(C)C1=C(C=CC=C1)C1N(CCNC1)C1CC2(C1)CCN(CC2)C(=O)OC(C)(C)C Chemical compound C(C)(C)C1=C(C=CC=C1)C1N(CCNC1)C1CC2(C1)CCN(CC2)C(=O)OC(C)(C)C WXSFUHRFTJTOCA-UHFFFAOYSA-N 0.000 description 5
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• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
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